When interactive computer technology is used in meaningful and connective ways, it both enhances and provokes the focus and purpose of art instruction and learning to be expansive and personally relevant. In this paper, we describe an approach to interpretation and curriculum design that requires users to make visual and conceptual associations among examples of visual culture, works of art, and content from various disciplines for the purpose of making meaning. A theoretical foundation for using hypertext authoring software to promote an empowering form of art education is provided, as are strategies for constructing rich interpretations of works of art and meaningful curricula. The use of hypertext authoring software by teachers and students to create interactive readings and on-going interpretations makes explicit their function as Type II applications. We believe that better ways of teaching and learning result from such interactive, hypertextual experiences with works of art, as they require users to make explicit various connections among various meaningful texts, experiences, and sources.